Patent GB-313110-A (GB)
Title: Process for the manufacture of azo-dyestuffs
IPC: C09B29/00
Filed: 1928-03-07
Abstract: 313,110. Carpmael, A., (I. G. Farbenindustrie Akt.-Ges.), March 7, 1928. Azo dyes; lakes.-Azo dyes containing substituted or unsubstituted arylhydroxy fatty acid residues attached to nitrogen atoms are made by coupling a diazo compound with a component which is substituted by the arylhydroxy fatty acid residue, or by coupling a diazotized phenylenediamine containing an arylhydroxy fatty acid residue attached to the second amino group or a derivative thereof, or by introducing the arylhydroxy fatty acid residue into an amino group of an azo dyestuff. They are suitable for discharge printing on wool and for the production of lakes. According to examples, (1) diazotized aniline is coupled with 1-phenoxyacetamino-8- hydroxynaphthalene - 3 : 6 - disulphonic acid. Instead of aniline, 2-aminobenzoic acid, 2-acetamino-5-aminoanisole, 4-amino-acetanilide or pxylidine may be used. The phenoxyacetyl residue may be replaced by the 2-(or 4)-chlorphenoxyacetyl-, the 2-(or 4)-nitrophenoxyacetyl-, the 2- chloro-4-methylphenoxypropionyl or the 1-(or 2-)- naphthoxyacetyl residue, and H acid by other aminonaphtholsulphonic acids or 1-ethylamino-8-hydroxynaphthalene-3 : 6-disulphonic acid. The dyestuff aniline # 1-(4<1>-chlorophenoxyacetyl-) - amino-8-hydroxynaphthalene - 4 : 6 - disulphonic acid dyes wool yellowish red. The dye-stuff aniline # H acid (alkaline), treated with phenoxyacetylchloride, yields the dyestuff first mentioned in this example. (2) The dyestuff 4-nitro-1-aminobenzene-2-sulphonic acid # 2- (#-amincethylamino)naphthalene-7-sulphonic acid is treated with 2-chlorophenoxyacetylchloride or the same final dyestuff is obtained from diazotized 4-nitro-1-aminobenzene-2-sulphonic acid coupled with 2-(#-2<1> -chlorophenoxyacetylaminoethylamino-) naphthatene-7-sulphonic acid. It dyes wool reddish violet. The dyestuff 4 : 6-dinitro-1-aminobenzene-2-sulphonic acid # 2-(#- 4<1>-methylphenoxyacetylaminoethylamino-) - naphthatene-6-sulphonic acid or 2-(#-5<1>chlor-2<1>-methylphenoxy - # - propionylaminoethylamino-) - naphthalene-7-sulphonic acid dyes wool reddish blue. (3) The dyestuff aniline-2 : 5-disulphonic acid # p-xylidine # 1-(4<1>-chlorophenoxyacetylamino)-8- hydroxynaphthalene 4 : 6-disulphonic acid gives a clear violet lake, and the dyestuff 4-chlor-2- anisidine # 1-(4<1>-chlorophenoxyacetylamino-)- 8-hydroxynaphthalene-4:6-disulphonic acid is a bluish red. (4) The dyestuff 4-amino-1-phenoxyacetylaminobenzene # 1-(4<1>-sulpho)-phenyl-3- methyl-5-pyrazolone dyes wool golden yellow. The phenoxyacetyl residue may be replaced by the 2-(or 4-)-chlorophenoxyacetyl-, the 2-(or 4-)- nitrophenoxyacetyl-, the #-(2-methylphenoxy-)- propionyl-, or the 1-(or 2)-naphthoxyacetyl residues. 2 - Amino - 4 - phenoxyacetylamino - 1 - methoxybenzene, 4 amino-2-N-methyl-N-phenoxyacetylamino-1-methylbenzene or 4-amino-1-N- ethyl-N-phenoxy-acetylaminobenzene, when diazotized and coupled with 2-methylamino-8-hydroxynaphthalene-6-sulphonic acid, give brown shades. Other pyrazolones, methylketol and its sulphonic acids or aminonaphthol sulphonic acids and their N-alkyl or acidyl substitution products may be used as coupling components. The nitro-group in the dyestuff 4-nitraniline # (4<1>-sulpho-)-1- phenyl-3-methyl-5-pyraxolone is reduced and treated with phenoxyacetylohloride. (5) The dyestuff 4-amino-1-phenoxyacetylamino-benzene # 1-naphthol-3 : 6-disulphonic acid dyes wool yellowish red. The dyestuff 2-(N-phenoxyacetylamino-N-ethyl)-1-aminobenzene # 2-naphthol- 6 : 8-disulphonic acid dyes wool orange. 4-Amino- (phenoxyacetylanilide)-3-sudphonic acid, 4-amino- (2<1>-naphthoxyacetylanilide)-3-sulphonic acid or 3 : 5-dichlor - 4 - amino-(phenoxypropionylanilide) may also be used as diazo components. Phenoxy, or naphthoxyacylated aminonaphthol sulphonic acids are prepared from the corresponding aminonaphthol sulpho acid and the corresponding substituted or unsubstituted phenoxy- or naphthoxy-acyl chloride. Substituted phenoxy- or naphthoxy-acetyl- or propionyl-chlorides are prepared by treating the corresponding acid with thionyl chloride. Substituted phenoxy- or naphthoxy-acetic or propionic acids are prepared from the sodium salts of the corresponding phenols or naphthols and the sodium salt of chloracetic or #-chloropropionic acid. 2-(#-Substituted phenoxyacetyl- or #-propionylaminoethylamino-)-naphthalene sulphonic acids are prepared from the corresponding 2-(#-aminoethylamino-)-naphthalene sulphonic acid and the corresponding substituted phenoxyacetyl- or #- propionyl-chloride. Phenoxy- or naphthoxyacetyl -1 : 4- or 1: 3- phenylene diamines are prepared by phenoxy- or naphthoxyacetylating the corresponding nitro aminobenzene followed by reduction of the nitro group, or from the diamino compound and one molecular part of the acetylating agent.